Amino-naphthalimido-sulphonic acid compounds and process of preparing same



Patented Mar. 10, 1931 UNITED STATES PATENT 'WILHELM ECKERT, OF FRANKFORT-ON-TH OFFICE E-MAIN-I-IOCHST, GERMANY, ASSIGNOR TO GENERAL ANILINE'WORKS, INC., OF NEW YORK, N. Y., A CORPORATION ,OF DELA- WARE AMINO-NAPHTHALIMIDO-SULZPHONIC ACID COMPOUNDS AND PROCESS OF PREPARING SAME No Drawing. Application filed April 4, 1929, Serial No. 352,606, and in Germany April 12, 1928.

My present invention relates to a process of preparing acid wool dyestuffs and to new products obtainable thereby.

I have found that acid wool dyestuffs of the kind described in my eopending U. S. application Ser. No.813,954 filed October 20, 1928, are obtainable by treating nitronaphthalic acid derivatives of the following general formula:

. N 04 co wherein X stands for hydrogen, alkyl, aralkyl or aryl in an aqueous solution with such reducing agents as simultaneously effect the entrance of a sulphonic acid group. Such agents are, for instance hydrosulfite, bisulfite or the like.

7 It is advantageous to add to the aqueous solution a water-soluble organic solvent, for instance, alcohol. The reaction, generally,

is carried out at boiling temperature, but it is also suflicient to heat the solution to a somewhat lower temperature.

It is also possible to use as parent materials such nitronaphthalic acid derivatives as contain a sulphonic acid group.

Inthis case the introduction of a further sulphonic acid group is unnecessary and it is sufficient to reduce the nitro group. As stated before, the'products obtainable by my process have been described partly in my copending application Serial No. 313,954. I wish to claim as new compounds in the present application the products of the general formula:

. 1 NH: wherein R stands for hydrogen or alkyl and X represents hydrogen or a metal, as for instance an alkali metal atom.

These products dye the animal fiber from 2m acid bath very evenand extremely clear ints.

The nitronaphthalic acid derivatives of the above given formula can be prepared either by oxydizing nitroacenaphthenes or by directly nitrating naphthalic anhydride (cf. Berichte der Deutschen Chemischen Gesellschaft vol. 82, page 3284) and subsequently condensing with ammonia, or a primary aliphatic or aromatic amine.

The following examples illustrate the invention, the parts being by weight unless otherwise stated:

(1) 10 parts of 4-nitro-naphthalic-N-meth ylimide of the following formula:

N o oo SOzNa and is a yellow crystalline powder which dissolves in water to a clear yellow solution with a strong greenish fluorescence. It dyes the animal fiber from an acid bath very even clear yellow tints.

parts ofhydrosulfite in 500 parts by volume 7 of waterand thewhole is subsequentlyheated e The dyestulf hi h in to boiling for some hours. 7

the form of its sodium-sLalt has thefollowing formula:

isolatedas indicated in Example' 'l. It is a -.yellowwater-soluble powder which dyes wool from an acid bath a yery clear, intense greenish yell'ow tint.

' .7130 parts of imam-1.8 h hane rsulfophenylimide of the formula are heated to boiling with 500'parts'by Volume of an aqueous hydrosulfite solution of about is filtered and after concentrating the filtrate 20 strength. After some hours'the solution the dyestufiisobtained by salting it outin f'the usualmanner. It dyes wool from an acid bath a Very clear yellow tint, r lI claim:

1. The process which comprises boiling a compound of the following general formula ' v ihereifi stands' forhydrogen, alkyl, ara1ky1 ..or.v.aryl with an aqueous. solution of hydro- 3 even and extremely clear tints. V

2. The process which comprises boiling a compound of the following general formula:

wherein X stands for hydrogen, alkyl, aralkyl or aryl with an aqueous solution of hydrosulfite in the presence of a water-soluble organic diluent.

3; The process which comprises boiling a compound of the following general formula:

wherein X stands for hydrogen, methyl or a substituted or unsubstituted benzene residue with an aqueous solution of hydrosulfite.

4:. The process wlrich 'comprises boiling a compound of the following general formula:

-wherein X stands for hydrogemwmethylor a substituted or msubstituted benzene residue with .an aqueoussolution of hydrosulfiite in the. presence ofla water-soluble organic diluent.

5. The process which comprisesiboiling #l-nitro-naphthalic-N-methyl-imide with an aqueous solution of hydro's'ulfite. e

6. The process which comprises boiling l-nitro-naphthalio-N-methyl-imide with an aqueous solution of hydrosulfite in the pres- .ence of a water-soluble organic diluent;

7. As new p roducts the compounds of the 1 following general formula:

wherein R stands for hydrogen or alkyl and X represents hydrogenor aimetal atom dye ingthe animal fiberfrom-an acid bath very 8. As a new product the compound of the following formula:

being a yellow crystalline powder dissolving in water to a clear yellow solution with a strong greenish fluorescence and dyeing the animal fiber from an acid bath a clear yellow tint.

9. As new products the compounds of the following general formula:

NH, wherein R represents hydrogen or alkyl and X stands for hydrogen or a metal, dyeing the animal fiber from an acid bath very even and extremely clear tints.

10. As a new product the compound of the following formula:

being a yellow water-soluble powder, animal fiber from an acid bath a clear ish yellow tint.

In testimony whereof, I afix my signature.

WILHELM EGKERT.

dyelng green- 

